HeyDrew! · 1 day ago
Director of Tax - (CPA)
Jacksonville, FL
Full-time
Onsite
Mid Level
$150K/yr - $210K/yr
4+ years expHeyDrew! is a Series A-funded startup focused on creating an AI tax strategy platform for small and medium-sized businesses. The Director of Tax will bridge compliance and AI-enabled tax strategy, leading the development of tax workflows and ensuring accurate, compliant returns while building a team of tax professionals.
Financial Services
No H1B
Responsibilities
Serve as the “Head of Learning” for our AI by translating tax strategies and IRC provisions into clear rules, workflows, and review standards
Codify high-value strategies (e.g., Augusta Rule, Accountable Plans, Section 179, R&D credits) into frameworks that the product and engineering teams can operationalize
Build and run the tax fulfillment organization, including “human-in-the-loop” review pods and the SOPs that make them efficient and consistent
Own quality assurance and compliance standards, ensuring returns meet Circular 230 expectations and internal quality gates
Operate the feedback loop: analyze where humans correct the AI and turn those learnings into updated guidance and rule improvements so issues don’t repeat
Drive efficiency over time by reducing manual oversight as automation improves (targeting meaningful decreases in human touch while maintaining accuracy)
Act as a strategic advisor for early customers (roughly 50–100), helping validate recommendations, build trust, and shape the service experience
Build a team of Senior CPAs, Enrolled Agents, Tax Research Team in time
Qualification
Required
Active CPA license (required)
4+ years of senior-level SMB tax experience, including S-Corps (1120-S), Partnerships (1065), and high-net-worth individual returns (1040)
2+ years of managing people (2 to 4 years is preferable)
Strong working knowledge of the IRC and how to apply tax strategy in real client scenarios
Collaborate with Senior Leadership and Partner with the Engineering Org
Experience leading teams and building repeatable processes (SOPs, quality checks, review workflows)
Comfort operating in a fast-moving startup environment and balancing speed with compliance risk
Tech-forward mindset; motivated by automation and scaling quality through systems (not just filing forms)
Strong judgment and ability to clearly explain tax logic to non-tax stakeholders (product, engineering, customer success)
Experience with hiring practices
Able to work in the office in Pontre Vedra 5 days a week
Able to work for any US Employer without any visa support now or in the future
Preferred
Experience in a TaxTech environment or leading change inside a traditional firm
Prior experience building or managing review “pods” or high-throughput tax operations
Experience working with AI-enabled tax tooling, automation, or process improvement initiatives
Experience working in an early-stage startup environment
Comfortable joining client strategy calls and representing the “voice of strategy” early on
Big 4 experience earlier in career
Benefits
Equity
Company
HeyDrew!
Most small businesses have a CPA who looks backward. At HeyDrew!, we give them an AI strategist that looks forward.
11-50 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase